Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acrylic Acid | HCID 6581 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | Methyl tryptophanate hydrochloride | HCID 2734891 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86655436 | HCID 86655436 | 28% |
Reaction Steps
Triethylamine (14 mL) was added to a chloroform (120 mL) solution of methyl L-tryptophanate hydrochloride (5.0 g) under ice-cooling, and further acrylic acid (1.6 mL) was added thereto. Next, a methylene chloride (30 mL) solution of DCC (4.9 g) was added dropwise to the mixture. The mixture was stirred at room temperature for 24 hours, and thereafter a half the volume of the solvent was distilled off under a reduced pressure, acetone was added to the residual mixture, and the mixture was allowed to stand in a freezer overnight. Triethylamine hydrochloride and DC urea were filtered off, the solvents of the filtrate was distilled off under a reduced pressure, and the residual oily product obtained was purified by silica gel column chromatography (BW-127ZH, chloroform:methanol=19:1), to give the captioned compound (1.5 g, 28%) as an oily product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09150510B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-4747f8035f25496aabf94370039ba808 |
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| Source note | uspto-grants-2015_10 |
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